Photochemical reactions of 1-methyl-4,6-diaryl-2(1H)-pyrimidinones in the presence of thiols
✍ Scribed by Takehiko Nishio; Michiyo Kato
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1997
- Tongue
- English
- Weight
- 181 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
Photochemical reactions of 1‐methyl‐4,6‐diaryl‐2(1__H__)pyrimidinones 1a‐b in the presence of thiols 2 are described. Irradiation of 1‐methyl‐4,6‐diaryl‐2(1__H__)‐pyrimidinones 1a‐b in benzene in the presence of thiols 2 gave the unexpected 2:1‐adducts, 3‐methyl‐4,6‐diaryl‐5‐aralkylthio‐6‐(1′‐methyl‐4′,6′‐diaryldihydro‐pyrimidin‐2‐on)yl‐1,3‐diazabicyclo[2.2.0]hexan‐2‐ones 3‐6, of 1 and 2, whereas irradiation of 1a‐b alone in benzene resulted in recovery of the unchanged 1a‐b.
📜 SIMILAR VOLUMES
## Abstract Irradiation of the 2(1__H__)‐pyrimidinones 1 in alcohols such as 2‐propanol and ethanol afforded the 1‐(alkoxycarbonylamino)‐3‐(arylimino)‐1‐propenes 4a–c, h and 2‐(alkoxycarbonylamino)‐4‐(arylimino)‐2‐pentenes 4d–g. These photoproducts are formed by trapping the isocyanate intermediate
The photochemical behaviour of 2-methyl-5-nitro-I H-imidazoles 1 in water-containing solutions has been studied. In a first reaction step, the photorearrangement of 1 yields 2-methyl-2-imidazoline-4,5-dione-4-oximes 2. Hydrolysis of 2 and subsequent elimination of water from a supposed intermediate